The Pocket ENT novel Kobayashi Maru, set in 2155, details the historical events which became the Academy simulation. Meanwhile, David Mack's novel A Time to Heal, Ensign Carmona identifies the Kobayashi Maru as having been lost in the Tezel-Oroko system, the location of the planet Tezwa, where most of this book occurs.

An updated version of the test was featured in Peter David's New Frontier book Stone and Anvil. In the book Elizabeth Shelby, then a cadet, was given the task of updating the scenario, with one of its first participants being Mackenzie Calhoun (also a cadet). In the updated version of the scenario the Klingons were replaced by Romulans, and an extra degree of difficulty was added with a radiation leak on the freighter. Calhoun's solution to it was to fire upon and destroy the freighter on the grounds that the Romulans were using it as bait to provoke an incident and possibly a war.

In The Q Gambit, Part 1, Nyota Uhura translates the word "Kobayashi" as "Smallwood", the name of the Federation civilian ship they encounter being attacked by Klingons (in reality, a test put forward by Q).

In the alternate universe, the Kobayashi Maru is visible on screen, albeit briefly.